The present invention relates to farnesene isomer mixtures containing, but not limited to, compounds defined according to the structures: ##STR1## and uses of such mixtures in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, medicinal products and toothpastes.
The compositions of our invention are prepared by dehydrating nerolidol compositions of matter containing their nerolidol isomers: ##STR2## using potassium bisulfate or paratoluene sulfonic acid dehydrating agents.
There has been considerable work performed relating to substances which can be used to augment or enhance flavors of foodstuffs, chewing gums, medicinal products and toothpastes. The substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
There has been considerable work performed relating to substances which can be used to augment or enhance flavors of foodstuffs. The substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Fresh green, herbaceous aroma and taste nuances are particularly desirable in several types of foodstuffs, e.g., citrus beverages, orange flavored ice creams and the like.
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)" at monograph 1378 discloses "Farnesal", 2,6,10-trimethyl-2,6,10-dodecatrien-12-al to have a very mild, sweet oily, slightly woody, tenacious odor. On the other hand, Arctander also describes, at Monograph 1379, Farnesene, 2,6,10-trimethyl-2,6,9,11-dodecatetraene defined according to the structure: ##STR3## to have a very mild, sweet and warm, rather nondescript odor of good tenacity. Arctander further states that apart from some possible use in the reconstruction of certain essential oils, there is to the author's knowledge, very little, if any, use for this sesquiterpene in perfumery as such. Arctander further states that Farnesene having the structure: ##STR4## is produced by dehydration of Farnesol by heat with a potassium dehydrating agent or from Nerolidol by heat with acetic anhydride.
Brieger, et al, J. Org. Chem. Volume 34, Number 12, December 1969, in their paper "The Synthesis of trans,trans-.alpha.-Farnesene" discloses dehydration of nerolidol using bisulfate at 170.degree. C. to yield a number of Farnesene isomers according to the reaction: ##STR5## Brieger, et al also discloses the dehydration of Farnesol using potassium bisulfate at 170.degree. C. as follows: ##STR6## Brieger also teaches the dehydration of Farnesol using potassium hydroxide at 210.degree. C. to yield certain isomers according to the following reaction: ##STR7##
Anet, Aust. J. Chem., 1970, 23, 2101-8, in a paper entitled "Synethesis of (E,Z)-.alpha.-, (Z,Z)-.alpha.-, and (Z)-.beta.-Farnesene" discloses the dehydration of (E)-nerolidol having the structure: ##STR8## in the presence of such dehydrating agents as phosphoryl chloride in pyridene to yield the compounds having the structures: ##STR9## according to the reaction: ##STR10##
In a paper by Hattori, et al entitled "Chemical Composition of the Absolute from Gardenia Flower" and in another paper by Tsuneya, et al entitled "GC-MS Analysis of Gardenia Flower Volatiles", it is disclosed that .alpha.-farnesene is existent in gardenia flower absolute. The Hattori, et al and Tsuneya, et al papers are published in the "VII International Congress of Essential Oils"; Japan Flavor and Fragrance Manufacturers' Association, Tokyo (1979) at pages 451 and 454, respectively (papers 128 and 129, respectively).
Nothing in the prior art cited above indicates the subject matter of our invention.